High-performance liquid chromatographic enantioseparation of unusual amino acid derivatives with axial chirality on polysaccharide-based chiral stationary phases

López-Ram-de-Víu, P. (Universidad de Zaragoza) ; Gálvez, J.A. (Universidad de Zaragoza) ; Díaz-de-Villegas, M.D.

Resumen: The successfulenantioseparationofaxiallychiralaminoacidderivativescontainingacyclohexylidene moiety onan an alyticalandsemipreparativescalewasachievedforthefirsttimebyHPLCusing polysaccharide-based chiral stationary phases. Racemicmethyl N-benzoylamino esters,easilyobtained by methanoly sisof the corresponding 5(4H)-oxazolones, were subject edtochiralHPLCresolutionusing chiral stationaryphasesbasedonimmobilized3,5-dimethylphenylcarbamatederivativesofamylose (Chiralpak® IA column)orcellulose(Chiralpak® IB column). The behaviour of both selectors under dif-ferent elution conditions was evaluated and compared. The amy los ecolumns howed better performance than the cellulose column for allenantiomers tested. These mi preparative resolution of axially chiral amino acidderivatives with different side chains has been achievedona 250mm×20mmIDChiralpak® IA columnusingtheappropriatemixtureof n-hexane/chlorofom/ethanol aseluent by successive injec-tions of asolution of the sample in chloroform. Using this protocol up to 120 m go feachenan tiomer of the correspondingaxiallychiralaminoacidderivativewereobtainedfrom300mgofracemate.[(Sa)-2a, 105 mg;(Ra)-2a, 60mg,[(Sa)-2b, 105mg;(Ra)-2b, 90mg,[(Sa)-2c, 120mg;(Ra)-2c, 100mg].

Idioma: Inglés

DOI: 10.1016/j.chroma.2015.02.055

Año: 2015

Publicado en: Journal of Chromatography A 1390 (2015), 78-85
ISSN: 0021-9673

Factor impacto JCR: 3.926 (2015)

Categ. JCR: CHEMISTRY, ANALYTICAL rank: 11 / 75 = 0.147 (2015) - Q1 - T1
Categ. JCR: BIOCHEMICAL RESEARCH METHODS rank: 14 / 77 = 0.182 (2015) - Q1 - T1

Factor impacto SCIMAGO: 1.693 - Analytical Chemistry (Q1) - Organic Chemistry (Q1) - Medicine (miscellaneous) (Q1) - Biochemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/GAE-102

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)